CPM-LAD

CPM-LAD
Clinical data
Other names	CPMLAD; CYPM-LAD; CYPMLAD; 6-(Cyclopropylmethyl)-6-nor-LSD; N(6)-Cyclopropylmethyl-norLSD;
Drug class	Serotonin receptor modulator; Serotonergic psychedelic; Hallucinogen
ATC code	None;
Identifiers
	IUPAC name (6aR,9R)-7-(cyclopropylmethyl)-N,N-diethyl-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinoline-9-carboxamide;
PubChem CID	166091837;
Chemical and physical data
Formula	C23H29N3O
Molar mass	363.505 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CCN(CC)C(=O)[C@H]1CN([C@@H]2CC3=CNC4=CC=CC(=C34)C2=C1)CC5CC5;
	InChI InChI=1S/C23H29N3O/c1-3-25(4-2)23(27)17-10-19-18-6-5-7-20-22(18)16(12-24-20)11-21(19)26(14-17)13-15-8-9-15/h5-7,10,12,15,17,21,24H,3-4,8-9,11,13-14H2,1-2H3/t17-,21-/m1/s1; Key:XTKDRKBVDJFYNW-DYESRHJHSA-N;

CPM-LAD, or CYPM-LAD, also known as 6-(cyclopropylmethyl)-6-nor-LSD, is a serotonin receptor modulator and putative psychedelic drug of the lysergamide family.¹²³⁴ It is the analogue of LSD in which the methyl group at the 6 position has been replaced with a cyclopropylmethyl group.¹²³

Use and effects

Unlike related lysergamides, CPM-LAD was not mentioned in Alexander Shulgin's 1997 book TiHKAL (Tryptamines I Have Known and Loved) and is not known to have been tested in humans.⁵

Interactions

Pharmacology

Pharmacodynamics

CPM-LAD showed affinity (K_i) values for serotonin receptors of 10.9 nM for serotonin-labeled 5-HT₁ receptors and 7.7 nM for ketanserin-labeled 5-HT₂ receptors.¹² These affinities were very similar to but slightly lower than those of LSD.¹² CPM-LAD fully substituted for LSD in rodent drug discrimination tests with an ED₅₀Tooltip median effective dose of 0.067 μmol/kg, relative to a dose of 0.046 μmol/kg in the case of LSD (with CPM-LAD about 1.5-fold less potent than LSD).¹² Additional pharmacology for CPM-LAD has also been published.⁴

History

CPM-LAD was first described in the scientific literature by Andrew Joseph Hoffman of the lab of David E. Nichols at Purdue University in 1987.³ Subsequently, it was patented by Gilgamesh Pharmaceuticals in 2022, who further studied and described its pharmacology.⁴ Derivatives of CPM-LAD have also been patented by Daniel Trachsel and Matthias Liechti and colleagues in association with MindMed.⁶

Society and culture

Legal status

Canada

CPM-LAD is not a controlled substance in Canada as of 2025.⁷

References

Pfaff RC, Huang X, Marona-Lewicka D, Oberlender R, Nichols DE (1994). "Lysergamides revisited" (PDF). NIDA Research Monograph. 146: 52–73. PMID 8742794.
Nichols DE, Oberlender R, McKenna DJ (1991). "Stereochemical Aspects of Hallucinogenesis". In Watson RR (ed.). Biochemistry and Physiology of Substance Abuse. Vol. 3. Boca Raton, Fla.: CRC Press. pp. 1–39. ISBN 978-0-8493-4463-3. OCLC 26748320. TABLE 1 Effects of N-(6)-Alkyl Subtituents on LSD-Like Behavior and Serotonin Receptor Affinity in Rats [...]
Hoffman AJ (1987). Synthesis and pharmacological evaluation of N(6)-alkyl norlysergic acid N,N-diethylamide derivatives (Ph.D. thesis). Purdue University. Retrieved 30 June 2025.
WO 2022226408A1, Kruegel AC, "Novel ergolines and methods of treating mood disorders", published 25 April 2022, assigned to Gilgamesh Pharmaceuticals, Inc. Example 13: Preparation of (6aR,9R)-N,N-diethyl-7-(cyclopropylmethyl)-4,6,6a,7,8,9-hexahydroindolo[4,3-fg]quinoline-9-carboxamide (13) [...]
Shulgin A, Shulgin A (September 1997). TiHKAL: The Continuation. Berkeley, California: Transform Press. ISBN 0-9630096-9-9. OCLC 38503252.
US 2023/0414583, Trachsel D, Liechti ME, Lustenberger F, "Lysergic acid derivatives with modified LSD-like action", published 28 December 2023, assigned to Mind Medicine Inc.
"Controlled Drugs and Substances Act". Department of Justice Canada. Retrieved 19 January 2026.

External links

CYPM-LAD - Isomer Design

[Pfaff_1994-1] Pfaff RC, Huang X, Marona-Lewicka D, Oberlender R, Nichols DE (1994). "Lysergamides revisited" (PDF). NIDA Research Monograph. 146: 52–73. PMID 8742794.

[Nichols_1991-2] Nichols DE, Oberlender R, McKenna DJ (1991). "Stereochemical Aspects of Hallucinogenesis". In Watson RR (ed.). Biochemistry and Physiology of Substance Abuse. Vol. 3. Boca Raton, Fla.: CRC Press. pp. 1–39. ISBN 978-0-8493-4463-3. OCLC 26748320. TABLE 1 Effects of N-(6)-Alkyl Subtituents on LSD-Like Behavior and Serotonin Receptor Affinity in Rats [...]

[Hoffman_1987-3] Hoffman AJ (1987). Synthesis and pharmacological evaluation of N(6)-alkyl norlysergic acid N,N-diethylamide derivatives (Ph.D. thesis). Purdue University. Retrieved 30 June 2025.

[WO2022226408A1-4] WO 2022226408A1, Kruegel AC, "Novel ergolines and methods of treating mood disorders", published 25 April 2022, assigned to Gilgamesh Pharmaceuticals, Inc. Example 13: Preparation of (6aR,9R)-N,N-diethyl-7-(cyclopropylmethyl)-4,6,6a,7,8,9-hexahydroindolo[4,3-fg]quinoline-9-carboxamide (13) [...]

[TiHKAL-5] Shulgin A, Shulgin A (September 1997). TiHKAL: The Continuation. Berkeley, California: Transform Press. ISBN 0-9630096-9-9. OCLC 38503252.

[US20230414583A1-6] US 2023/0414583, Trachsel D, Liechti ME, Lustenberger F, "Lysergic acid derivatives with modified LSD-like action", published 28 December 2023, assigned to Mind Medicine Inc.

[CDSA-7] "Controlled Drugs and Substances Act". Department of Justice Canada. Retrieved 19 January 2026.

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